Tuesday, December 2, 2025

The Best Ankle-Boot Trend to Wear With Dresses This Winter

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You can always count on Suki Waterhouse to add her signature boho twist to whatever outfit she’s wearing, and that’s exactly what she just did. In this case, it was via her shoes. For obvious reasons, dresses are typically put on the back burner this time of year, but if you choose to wear one anyway, despite the cold, you’re probably going to want to wear boots with it. So, let’s discuss the type of boots.

There’s been much discussion about whether ankle boots are out or in, but I see them as a staple. That said, there are certainly types of ankle boots that can look a bit dated, so if they’re going to be on full display, with, say, a mini dress, you want to choose a trend-forward style such as Waterhouse’s. With her black leather jacket and pastel mini dress, she opted to wear a pair of slouchy ankle boots. Slouchy boots made a strong comeback this fall, with the fashion crowd pairing them with dresses, skirts, and jeans. The effortless look of the trend was the perfect match for Waterhouse’s simple leather-jacket-and-mini-dress outfit, so I highly suggest styling slouchy ankle boots just as she did while out in NYC this week.

Keep scrolling to shop Suki Waterhouse‘s chic boho-inspired dress outfit combination, along with a handful of other slouchy ankle boots that are perfect with dresses and everything else.

Suki Waterhouse wearing a black leather jacket, mini dress, and slouchy ankle boots

(Image credit: TheStewartofNY/GC Images/Getty Images)

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